Really, you've articulated my actual, underlying desire (i.e. Getting More Awesome) quite well in the OP. Why don't you have a go at articulating your "nebulous" thoughts. Consider it brainstorming, don't worry about it being neat or perfect!

I think that pick-up artistry is a really limited subset of social fitness, if it even applies at all.

Sure, but that's irrelevant. I just think they've provided a decent example of a group getting together to figure out how to work on a particular social skill. In the article I linked, I was advocating copying their learning methods, nothing more.

ETA: Well, this is certainly timely!